Thionyl Chloride → 6-(3,6-dichloro-pyridazine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

HRID 469324

反応式

HRID 469324 の反応式
S(Cl)(Cl)=O.[Cl:5][C:6]1[N:7]=[N:8][C:9]([Cl:15])=[CH:10][C:11]=1[C:12](O)=[O:13].[Cl-].[Cl-].[Cl-].[Al+3].[CH3:20][C:21]1[C:26]2[NH:27][C:28](=[O:30])[O:29][C:25]=2[CH:24]=[CH:23][CH:22]=1>ClCCCl>[Cl:5][C:6]1[N:7]=[N:8][C:9]([Cl:15])=[CH:10][C:11]=1[C:12]([C:23]1[CH:22]=[C:21]([CH3:20])[C:26]2[NH:27][C:28](=[O:30])[O:29][C:25]=2[CH:24]=1)=[O:13]

参加物

6

反応物 4

HCID 24386Thionyl ChlorideHCID 4338043,6-Dichloropyridazine-4-carboxylic acidHCID 6451240Aluminum(III) ChlorideHCID 127093364-Methyl-3H-benzooxazol-2-one

生成物 1

HCID 581811846-(3,6-dichloro-pyridazine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
100 °C

実験手順

2.00 mL (27.4 mmol) thionyl chloride were added to 1.92 g (9.95 mmol) 3,6-dichloro-pyridazine-4-carboxylic acid in 10 mL 1,2-dichloroethane and the mixture was refluxed for 2 h. The reaction mixture was evaporated to dryness and coevaporated with 1,2-dichloroethane. Then 5.30 g (39.8 mmol) aluminium trichloride and 1.56 g (10.5 mmol) 4-methyl-3H-benzoxazol-2-one were added and the mixture was stirred for 1 h at 100° C. under a nitrogen atmosphere. Then it was stirred for a further 2 h at 120° C., 3 h at 130° C. and then cooled for 48 h at RT. The mixture was decomposed with ice water and extracted with DCM. The organic phases were combined, washed with water, dried on sodium sulphate, filtered and evaporated down i. vac. The residue was triturated with DIPE, suction filtered and dried.

後処理

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe reaction mixture was evaporated to dryness
  3. stirringThen it was stirred for a further 2 h at 120° C., 3 h at 130° C.
  4. temperaturecooled for 48 h at RT
  5. extractionextracted with DCM
  6. washwashed with water
  7. customdried on sodium sulphate
  8. filtrationfiltered
  9. customevaporated down i
  10. customThe residue was triturated with DIPE, suction
  11. filtrationfiltered
  12. customdried

出典と根拠

ORDレコード
ord-cc30edbc4c1543d59c80220e9fc8cade
出典データセット
uspto-grants-2014_01
特許番号
US08629137B2

関連ノート

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